Joel Lindsey

In the 2000s, when he wasn’t shagging starlets or performing stand-up comedy, artist was leveraging his two distinct gifts: His virtuosic guitar skills and his aptitude for classy pop-rock songs. Putting those abilities to use both on his solo albums and with the band, his blues-rock group, the artist earned big chart success, becoming the sensitive singer-songwriter of choice for hordes of Americans.

The middle son of two teachers who grew up in Fairfield, CT, he picked up guitar at age 13 and was soon playing local blues clubs both solo and with the band Villanova Junction. At 17, he suffered a cardiac arrhythmia that kept him hospitalized for a week. It was then that his songwriting career began in earnest. A year after finishing high school, the artist enrolled at Boston’s Berklee College of Music on a partial scholarship. He dropped out after his first year to move to Atlanta and play live with his friend Clay Cook under the name LoFi Masters. He left the duo to record his first EP, 1999’s Inside Wants Out, which he distributed himself while playing gigs across the South.

His big break came after he appeared at 2000’s South by Southwest Music Festival in Austin, TX, when he signed with Aware Records, a Columbia subsidiary. His first full-length album, Room for Squares (Number 8, 2001) was picked up by Columbia for wide release. Room for Squares went multi-platinum on the back of singles “No Such Thing” (Number 13, 2002) and “Your Body Is a Wonderland” (Number 18, 2002). Columbia followed that success by reissuing Inside Wants Out in late 2002.

Around the same time, Mayer began to branch our musically as well. He provided backing vocals on rapper Common’s single “Go!” and shared the songwriting credit with Common and Kanye West. In his own music, Mayer began to focus on meatier stuff, particularly the blues. He played shows with Buddy Guy and Herbie Hancock, and in November 2005 released another live album, Try! (Number 34), credited to the John Mayer Trio, which included veteran session musicians Steve Jordan on drums and Pino Palladino on bass.